WO1989009418A1 - Lentille en plastique - Google Patents

Lentille en plastique Download PDF

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Publication number
WO1989009418A1
WO1989009418A1 PCT/JP1989/000345 JP8900345W WO8909418A1 WO 1989009418 A1 WO1989009418 A1 WO 1989009418A1 JP 8900345 W JP8900345 W JP 8900345W WO 8909418 A1 WO8909418 A1 WO 8909418A1
Authority
WO
WIPO (PCT)
Prior art keywords
plastic lens
mold
copolymer
plastic
weight
Prior art date
Application number
PCT/JP1989/000345
Other languages
English (en)
Japanese (ja)
Inventor
Shigeo Nakamura
Original Assignee
Hoya Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoya Corporation filed Critical Hoya Corporation
Priority to DE68920554T priority Critical patent/DE68920554T2/de
Priority to JP1503809A priority patent/JP3043024B2/ja
Priority to EP89904205A priority patent/EP0371140B1/fr
Publication of WO1989009418A1 publication Critical patent/WO1989009418A1/fr

Links

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses

Definitions

  • the present invention relates to a plastic lens, and more particularly to a high refractive index plastic lens suitable as an eyeglass lens. ⁇ Technology
  • methyl alcohol monomer (DEBAC) monomer and methyl methacrylate acrylate (: MMA) monomer are A plastic lens for eyeglasses is manufactured by injecting into a mold or the like and then overlapping. These plastic lenses are lighter, safer and more dyeable than conventional inorganic glass lenses (Clara Glass Lenses). Excellent in terms of aspect. Tooth ⁇ , refractive Oriritsu (n D) of the come are these-flops La scan switch click-les-down figure Ri Ah at about 5 0, refractive Oriritsu of conventional inorganic glass La Threshold Level emissions's (N D) It is smaller than 1.5 2 3 and the plastic lens has the drawback that the center thickness and the edge thickness must be increased for this purpose. There is a demand for the development of plastic lenses with a high refractive index in order to remedy such drawbacks.
  • DEBAC methyl alcohol monomer
  • MMA methyl methacrylate acrylate
  • the high refractive index plastic lens obtained in this way not only has a high refractive index, but also has physical and chemical properties as an eyeglass lens. It is also required that they are good and have good moldability.
  • Plastic lenses satisfying these conditions include, for example, a jet lens disclosed in Japanese Patent Application Laid-Open No. 57-212401. Glyco-Visor Reynolds (DEBAC), Glyphal Phthalate (DAP), and Peng Revolution (BzMA) ) And a plastic lens made of a terpolymer, and the plastic lens is disclosed in Japanese Unexamined Patent Publication No.
  • a DEGBAC, DAP and BzMA monomer mixture is made of glass or metal.
  • Prior art copolymer prepared by the method of the above have a high refractive index (n D l. 5 about 5), but also physical chemical 'properties are good good and moldability Ru Nodea
  • the monomer mixture is poured into a mold assembled with molds and gaskets. In this case, the monomer mixture easily adheres to the outer surface of the mold, and if heat curing is performed in this state, the monomer mixture adhering to the mold will be heated. As a result, the outer surface of the mold becomes contaminated with the adhered semi-hardened viscous liquid.
  • the DEGBAC-DAP-BzMA copolymer can be used for molding and molding.
  • the adhesiveness of the copolymer is weak, and it is better than the mold and gasket containing the copolymer in the cleaning mixture of methylene chloride and strong alkali. After removing only the gasket from the mold, if it is immersed, a separation will occur between the copolymer and the mold. As a result, the cleaning liquid enters the mold and the plastic lens surface is roughened by the cleaning liquid, causing a dripping phenomenon, clouding, and striae. There were easy drawbacks.
  • the purpose of the present invention is to improve the adhesion to the mold, so that even if it is immersed in the above-mentioned cleaning solution, surface dripping, clouding, and pulse due to separation-shortening occur.
  • the aim is to provide a high refractive index plastic lens that does not cause any problems. Disclosure of the invention
  • each monomer constituting the plastic lens is in the above-mentioned specific composition range. Is required. That is, the composition range of the component (A), diethyl carbonate, bisulfuric acid carbonate (DEGBAC), is 5 to 40% by weight. %. The reason is that if the content exceeds 40% by weight, the physical and chemical properties (eg, scratch resistance, impact resistance, solvent resistance, weather resistance, etc.) are improved, but the bending is not easy.
  • n D Ri cloudy in Les down's, striae good or to be with Les emissions's glasses
  • Ri Do Ni Let 's that are sure Me et al. If the content is less than 5% by weight, the physical and chemical properties are deteriorated, the formability is reduced, and the practicality is degraded. .
  • the composition range of benzyl methacrylate (BzMA), which is the component (B), is 5 to 40% by weight. The reason is that if it exceeds 40% by weight, cloudiness, striae are observed, and the moldability becomes very poor, and 5% by weight. If the amount is not too low, the lens power is less than the yellowing power. Also
  • the component (C), the girder phthalate (DAP), is a gallary oleophthalate (DAIP), a gyroreletter phthalate (DATP) Alternatively, these mixtures may be used, and the composition range of the DAP is 14 to 88% by weight. The reason is that if it exceeds 88% by weight, the physical and chemical properties and formability deteriorate, and if it is less than 14% by weight, the refractive index becomes low. These are the forces that decrease the temperature, make the lens cloudy, have striae, and deteriorate the formability. Alkyl alkyl acrylates having 1 to 4 carbon atoms in the anol group, which is the component (D)
  • AMA includes: methyl methacrylate, ethyl methacrylate, propyl methacrylate, and metal methacrylate. It can be used for at least one kind of power selected from Chinore Meteor Crater, Rare Group Power.
  • propylmethacrylate includes n-propylmethacrylate and i- propylmethacrylate, but The relays include n-butyl methacrylate, i-butyl methacrylate, and t-butyl methacrylate.
  • the composition range of AMA is 2 to 6% by weight.
  • the reason is that, if it exceeds 6% by weight, the adhesion between the copolymer and the mold becomes too strong, so that it becomes too difficult to release the mold and the dyeability decreases. If the content is less than 2% by weight, adhesion between the copolymer and the mold is weak, and the copolymer is immersed in a cleaning solution such as a mixed cleaning solution of methyl chloride and strong aluminum. When this is done, separation is likely to occur between the copolymer and the mold, and the copolymer is immersed in the cleaning solution as described above, and the plastic is immersed. These are the forces generated on the surface of the lens.
  • the plastic lens of the present invention is obtained by mixing the component (A), the component (B), the component (C) and the component (D) so as to have the above specified weight composition, A polymerization initiator is added to the mixture, and the mixture is mixed with a glass mold and a resin mold.
  • the polymer By pouring into the mold assembled by the skewers and polymerizing using a means such as heating or UV irradiation, the polymer is hardened. can get .
  • the polymerization may be performed as described above.
  • the polymerization initiator various known ones can be used, but it is appropriately selected according to desired reaction conditions (temperature, time, etc.). For example, 1, 1 azo biscyclohexane carbonate, jisopropyl peroxy car carbonate, 1, 1'- Azobiscyclohexyl nitrate, j-tert-butyl nonoxide, and the like are suitable.
  • UV absorber various well-known substances can be used, for example, 2,2'-dihydroxy-141-methoxybenzophenone. , 2 — (2′-one-high-opening mouthpiece 1 5 ′ -tert-octanol phenol) benzotriazole and the like are suitable.
  • the plastic lens of the present invention is a polyethylene glycol with a predetermined composition range.
  • the copolymer force obtained by copolymerizing a monomer mixture obtained by adding an alkylene monomer (AMA) of a predetermined composition range to a monomer mixture for use in This copolymer has excellent adhesiveness to the mold, for example, it has a high methyl chloride strength. Even if it is immersed in a cleaning solution such as a mixed cleaning solution, it is possible to prevent the presence of seno between the copolymer and the mold. Without the force of the laser, the conventional DEGBAC—BzMA—DAP-based plastic lens had a problem with the surface blemishes and striae. The occurrence is prevented.
  • the basic monomer composition is composed of DEGBAC, BzMA and DAP, it is said that it has high refractive index, good physical and chemical properties, and good moldability. Retains the features of conventional DEGBAC-BzMA-DAP plastic lenses.
  • the monomer was polymerized by heating and heating from 40 ° C. to 90 ° C. over 24 hours.
  • the monomer mixture adhering to the outer surface of the mold was partially polymerized and turned into a viscous liquid.
  • a plastic lens consisting of a hardened quaternary polymer was removed from the mold, and further heat-treated at 12 ° for 1 hour.
  • the component (A) is DEGBAC
  • the component (B) is BzMA
  • the component (C) is The composition ratio of DAP (01 or 0?)
  • AMA MMA or n-BuMA (n-butyl methacrylate)] which is the component (D) is defined by the present invention.
  • a plastic lens was manufactured in the same manner as in Example 1 except that the temperature was varied as shown in Table 1A within the above range.
  • Table 1B shows the physical properties of each plastic lens obtained.
  • MMA Methyl methacrylate
  • BuMA n-butyl methacrylate
  • Table 1B Refractive index Transmittance Seno II.
  • Refractive index Based on Abago refractometer manufactured by Atago.
  • Transmittance According to a day spectrophotometer.
  • the plastic lens of the present invention has excellent physical and chemical properties which the conventional high refractive index plastic lens has. It retains its properties and formability as it is, and has the drawbacks of conventional high refractive index plastic lenses: surface sagging, fogging and striae. For example, it is suitably used as an eyeglass lens.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La lentille en plastique ci-décrite est préparée à partir d'un copolymère obtenu par copolymérisation d'un mélange de monomères que l'on prépare en ajoutant du méthacrylate d'alkyle présentant une composition déterminée à un mélange de monomères habituel pour lentilles en plastique, composé de carbonate de bis-allyle diéthylène glycol, méthacrylate de benzyle et phtalate de diallyle, ayant chacun une composition déterminée. Ce copolymère présente une forte adhésion à un moule, et il ne se produit pas de séparation entre le copolymère et le moule même lorsqu'on les plonge dans une solution de lavage telle qu'un mélange de chlorure de méthylène avec un alcali fort. Cette composition permet d'éviter les désavantages présentés par les lentilles en plastique habituelles, à savoit les ondulations ou le ternissement en surface et la formation de stries.
PCT/JP1989/000345 1988-03-31 1989-03-31 Lentille en plastique WO1989009418A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE68920554T DE68920554T2 (de) 1988-03-31 1989-03-31 Kunststofflinse.
JP1503809A JP3043024B2 (ja) 1988-03-31 1989-03-31 プラスチック レンズ
EP89904205A EP0371140B1 (fr) 1988-03-31 1989-03-31 Lentille en plastique

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8012688 1988-03-31
JP63/80126 1988-03-31

Publications (1)

Publication Number Publication Date
WO1989009418A1 true WO1989009418A1 (fr) 1989-10-05

Family

ID=13709527

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1989/000345 WO1989009418A1 (fr) 1988-03-31 1989-03-31 Lentille en plastique

Country Status (5)

Country Link
US (1) US5130393A (fr)
EP (1) EP0371140B1 (fr)
AU (1) AU606277B2 (fr)
DE (1) DE68920554T2 (fr)
WO (1) WO1989009418A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100438000B1 (ko) * 2001-06-18 2004-06-26 에스에스씨피 주식회사 플라스틱 광학렌즈용 수지 조성물

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3266162B2 (ja) * 1992-08-26 2002-03-18 昭和電工株式会社 光学材料用組成物
TW385317B (en) * 1995-02-12 2000-03-21 Akzo Nobel Nv Ophthalmic lenses
JP3969609B2 (ja) * 1997-09-17 2007-09-05 Ｈｏｙａ株式会社 プラスチックレンズ用注型成形材料およびプラスチックレンズの製造方法
US6060439A (en) * 1997-09-29 2000-05-09 Kyzen Corporation Cleaning compositions and methods for cleaning resin and polymeric materials used in manufacture
WO1999038899A1 (fr) 1998-01-30 1999-08-05 Ppg Industries Ohio, Inc. Composition polymerisable a base de polyol(allyl-carbonate)
US6925068B1 (en) * 1999-05-21 2005-08-02 Wi-Lan, Inc. Method and apparatus for allocating bandwidth in a wireless communication system
JP4117231B2 (ja) * 2003-08-05 2008-07-16 Ｈｏｙａ株式会社 プラスチックレンズ及びその製造方法
EP3282290B1 (fr) 2016-08-09 2018-10-17 Essilor International Composition pour la fabrication d'une lentille ophtalmique comprenant un additif absorbant la lumière encapsulé

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51125487A (en) * 1975-03-26 1976-11-01 Japan Atom Energy Res Inst Aprocess for producing transparent plastic shaped articles

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5441965A (en) * 1977-09-09 1979-04-03 Asahi Glass Co Ltd Manufacture of optical element
JPS5661411A (en) * 1979-10-25 1981-05-26 Hoya Corp High refractive-index terpolymer with good dyeing property
JPS57212401A (en) * 1981-06-24 1982-12-27 Hoya Corp High refractive index plastic lens
AU541940B2 (en) * 1981-10-22 1985-01-31 Hoya Lens Corporation Bisallyl carbonate terpolymer
JPS6044327B2 (ja) * 1983-04-13 1985-10-03 テイジンレンズ株式会社 高屈折率レンズ用樹脂の製造法
JPS60197709A (ja) * 1984-03-19 1985-10-07 Ito Kogaku Kogyo Kk 光学部品用有機ガラス
EP0305048A3 (fr) * 1987-08-27 1990-05-09 Sola International Holdings, Ltd. Lentilles et préformes de lentilles préparées d'un copolymère

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51125487A (en) * 1975-03-26 1976-11-01 Japan Atom Energy Res Inst Aprocess for producing transparent plastic shaped articles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0371140A4 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100438000B1 (ko) * 2001-06-18 2004-06-26 에스에스씨피 주식회사 플라스틱 광학렌즈용 수지 조성물

Also Published As

Publication number Publication date
AU3357689A (en) 1989-10-16
EP0371140A1 (fr) 1990-06-06
EP0371140A4 (en) 1991-01-30
EP0371140B1 (fr) 1995-01-11
AU606277B2 (en) 1991-01-31
US5130393A (en) 1992-07-14
DE68920554D1 (de) 1995-02-23
DE68920554T2 (de) 1995-06-22

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